(2R,3S,4S,5R,6S)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-(pent-4-en-1-yloxy)tetrahydro-2H-pyran

Base Information

• Chemical Name: (2R,3S,4S,5R,6S)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-(pent-4-en-1-yloxy)tetrahydro-2H-pyran
• CAS No.: 125392-60-1
• Molecular Formula: C₃₉H₄₄O₆
• Molecular Weight: 608.775
• Mol file: 125392-60-1.mol

Synonyms:(2R,3S,4S,5R,6S)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-(pent-4-en-1-yloxy)tetrahydro-2H-pyran

Chemical Property of (2R,3S,4S,5R,6S)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-(pent-4-en-1-yloxy)tetrahydro-2H-pyran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,4S,5R,6S)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-(pent-4-en-1-yloxy)tetrahydro-2H-pyran

There total 4 articles about (2R,3S,4S,5R,6S)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-(pent-4-en-1-yloxy)tetrahydro-2H-pyran which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

n-Pent-4-enyl alcohol (821-09-0) + phenyl (2,3,4,6-tetra-O-benzyl)-1-thio-β-D-galactopyranoside S-oxide (117307-18-3) → (2R,3S,4S,5R,6R)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-(pent-4-en-1-yloxy)tetrahydro-2H-pyran (131684-77-0) + (2R,3S,4S,5R,6S)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-(pent-4-en-1-yloxy)tetrahydro-2H-pyran (125392-60-1)

Guidance literature:

With gold(III) chloride; silver trifluoromethanesulfonate; In dichloromethane; at 35 - 39 ℃; for 0.416667h; Overall yield = 62 %; Overall yield = 56 mg; diastereoselective reaction; Inert atmosphere; Molecular sieve;

DOI:10.1016/j.carres.2016.11.012

Reference yield:

D-Galactose (10257-28-0) → (2R,3S,4S,5R,6S)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-(pent-4-en-1-yloxy)tetrahydro-2H-pyran (125392-60-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 37 percent / H2O / 24 h / 50 °C / α-D-galactosidase

2: 1.) NaH / 1.) DMF, 0 deg C, 30 min, 2.) DMF, from 10 deg C to 20 deg C, 4 h

With sodium hydride; In water;

DOI:10.1016/0957-4166(96)00238-8

Reference yield:

n-Pent-4-enyl alcohol (821-09-0) → (2R,3S,4S,5R,6S)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-(pent-4-en-1-yloxy)tetrahydro-2H-pyran (125392-60-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 37 percent / H2O / 24 h / 50 °C / α-D-galactosidase

2: 1.) NaH / 1.) DMF, 0 deg C, 30 min, 2.) DMF, from 10 deg C to 20 deg C, 4 h

With sodium hydride; In water;

DOI:10.1016/0957-4166(96)00238-8

upstream raw materials:

benzyl bromide

pent-4-enyl O-α-D-galactopyranoside

D-Galactose

n-Pent-4-enyl alcohol

Downstream raw materials:

methyl 4-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-2,3,6-tri-O-benzoyl-α-D-galactopyranoside